If you follow me on instagram, you already know that this weekend I set off on my first solo travel adventure. After interviewing these lovely ladies, I figured it was about time. I also needed to cross #4 off my 25 for 25. A Spirit flight to Chicago was the cheapest option I could find (just $68 roundtrip!) so I booked it and waited until the very last minute to make my plans. They essentially formed on the go, with the help of some really awesome Skimm’bassadors (what you don’t get the Skimm? Sign up here) and friends.

I woke up at 3 am Saturday morning to prep and arrive for my 6 am flight out of BWI. When I arrived at the airport, I scrolled through some recommendations and booked a room at the Freehand. It is located just a few blocks off the Magnificent Mile and a 10 minute walk north of Millenium Park. I booked an adorable little private at $92 a night but they also offer more budget-friendly dorm accommodations. A great option for solo travelers looking to meet people. The hotel was easy to get to from O’Hare using the L train. I also used the train a few times to get to other neighborhoods like Lakeview, Wrigleyville and Lincoln Park. When I arrived at the Freehand, my room was ready so I dropped off my things and grabbed avocado toast at their cafe downstairs before heading out.

Magnificent Mile

After leaving the hotel, I walked south along the Magnificent Mile – a mile of shops lining Michigan Avenue. I recognized most of the brands but decided not to shop since I only packed a small backpack for the entire trip. I did stop into Dylan’s Candy Bar on my last day to pick up a few fun flavored chocolate bars to share back home. Heading south in the morning, the sun ends up cutting through the buildings at an angle that makes them shine. I couldn’t help but stop and take some photos near the Chicago river. Everything gleamed blue and white in the fresh morning light.

Millenium Park + The Bean

Continuing south on Michigan Ave, Millenium Park is only a few blocks south of the Chicago River. It’s impossible to miss. I wanted to see the famous bean, and after following the general flow of pedestrian traffic, I came up on it in no time. In the winter they have a large Christmas tree and an ice skating rink set up in the park. There are also a variety of sculptures and gardens to see. Across the street (towards the lake) there’s also the Maggie Daley park, worth exploring. I got the best view of the bean when I visited at 7 am on my last day. For awhile, another photographer and I were the only ones there. We chatted, snapped touristy pictures and exchanged stories until our fingers froze.

Lakefront

Walking east of Millenium Park, I landed right on the shore of Lake Michigan. From within the city it’s easy to forget the waterfront even exists, but once you find it, it becomes the foreground of the cityscape. One path lined with benches runs along the water while another path lies just outside of that, providing lanes for runners and bikers.

Adler Planetarium

The gentleman working at the front desk told me one of the best views of the city skyline is from the planetarium. Once I found the lakefront, I followed it south until I landed at the planetarium. He was right, from there I could take in the whole skyline and got some stunning photographs. The water and lake were surprisingly blue.

Shedd Aquarium

The planetarium is just past the aquarium. I doubled back to check on the wait but decided I’d try back later. I was hungry and didn’t have the patience to wait for the entrance. Tickets cost $8 for general admission when you purchase them on site, but there are also a bunch of other bundle packages you can buy online if you plan on visiting the other popular museums and sites as well.

Giordano’s Deep Dish

When I arrived at Giordano’s it was a mad house. They cook each pie to order so it takes about an hour and I ordered mine to go at the carryout counter to beat the long wait. When my pie was ready I picked it up and walked back into the park to eat at one of the picnic tables. Giordano’s pizzas are stuffed with cheese. The pizza was delicious but I went into an immediate food coma.

Christkindlmarket

Saturday evening I met up with one of the Chicago Skimm’bassadors, Brittany and we explored the Christmas Market together. It was definitely crowded but the line for spiced wine didn’t take as long as expected. And they serve the warm beverages in a fun little boot mug you can take home. Entering the market is free and there’s a good variety of German foods and crafts for sale inside. There’s also a crepe stand, usually set up at the French market, just outside the entrance. I went back Sunday for a warm nutella crepe.

Southport Grocery + Cafe

Sunday morning I woke up and took the L train north to the Belmont stop. From there I wandered through Lakeview and made my way to the Southport Grocery and Cafe for brunch with my friend Liz. The goodies for sale look delicious but the menu is even better. They serve cupcake batter pancakes and grown up pop tarts for sharing. And they’re famous for their bread pudding pancakes. We both prefer savory breakfast dishes so we settled on the hash and couldn’t have been happier. Since I had taken the train all this way I decided to take some time and wander around Wrigleyville and Boyston after brunch.

Lincoln Park Zoo

In the afternoon I met one of my oldest friends, Katie near her apartment in Lakeview and we walked towards the Lincoln Park Zoo. Right across the street we stopped at the J. Parker, the rooftop bar at the Lincoln Hotel, for some beautiful views of the city looking out over Lake Michigan. It’s a great spot for grabbing happy hour drinks in the summer, but they add a glass top in the winter so you can stay warm and still take in the views. The zoo is a fun place to walk around, offers great views of the city skyline and is free to enter!

Virgin Hotel

Sunday night I tried to go to the rooftop at the Chicago Athletic Association but it was closed for a private event. Next on my list was the rooftop bar at the Virgin Hotel. It’s on the 26th floor and offers some nice views of the immediate surrounding skyline. The staff were super friendly and chatted with me for awhile about my solo adventure and other travels.

Eataly

Before calling it a night I stopped in at Eataly, next door to my hotel. It’s heaven for foodies and winos alike. Grab a glass and wander from counter to counter until you spot something you’d like to eat. They also offer all sorts of home goods and products to go. I could have easily spent the whole day here sampling cheese and wine.

Navy Pier

Monday morning I woke up at 6 am to get views of the empty city and the hopes of a sunrise. It turned out to be so foggy that I couldn’t see the top of the building right in front of me. On a clear day the Navy Pier offers a great view of the city skyline from over Lake Michigan. Since I couldn’t make out any skyline I headed back into the city and got some uninterrupted views of the Bean and Millenium Park before any other tourists rose from bed.

Chicago 360 + Signature Room

The last site on my to do list was to visit the Signature Room on the 96th floor of the John Hancock building. It’s the “free” alternative – just buy a drink – to Chicago 360 on the 95th floor (usually $20 to enter). I was told the best views were from the ladies room in the Signature Room. I got there too early and couldn’t wait until it opened at 11 so I paid to go up to the 95th floor. Since it was so foggy I only had to pay $10, the limited visibility rate.

Pequod’s

On my way to the airport I picked up a cheese deep dish from Pequod’s. I had received a few recs claiming this pie as their favorite so I knew I had to give it a try. I called in my order in advance since deep dish pizzas take so long to bake! Personally, I prefered Giordano’s but to be fair I did fly all the way home with the pizza and reheat it in the oven before eating it. I’m sure it’s best fresh!

It was a whirlwind of a weekend but I had so much fun exploring Chicago. Now I can’t wait to go back when the weather is warm. Did I miss any of your favorite spots around the city?

Want to take your own trip? Get my budget for the weekend here.